Tom Brady and Bridget Moynahan’s relationship had its fair share of ups and downs.

When the pair were first linked in early 2004, they were both experiencing career highs. Brady had just won his second Super Bowl as quarterback for the New England Patriots, while Moynahan had famously appeared on Sex and the City and starred in films including Coyote Ugly, Serendipity and The Recruit.

With their careers soaring, their relationship took off as well. Brady and Moynahan were seen at high-profile red carpet events like the 2005 Vanity Fair Oscars party and the Met Gala. They also supported one another at movie premieres and championship ring ceremonies.

After three years together, the pair surprised fans when they announced their split in December 2006. Two months later, Moynahan’s rep confirmed that the actress was pregnant — and that Brady was the father. But despite rumors of tension and drama between Moynahan, Brady and his then-new girlfriend Gisele Bündchen, the former couple has mastered the art of peaceful co-parenting over the years.

“From the very beginning the whole goal specifically was to always keep it positive,” Moynahan told PEOPLE about co-parenting with Brady in 2019. “To raise a son in the healthiest environment, and I know we’ve all done that, and it shows.”

February 1, 2004: Tom Brady celebrates his Super Bowl win with Bridget Moynahan

Following Super Bowl XXXVIII, where the New England Patriots defeated the Carolina Panthers, Brady celebrated with his team — and his new girlfriend Moynahan. Sports Illustrated reported that Moynahan was first to arrive at the victory party, and the couple were affectionate with each other throughout the night.

April 13, 2004: Tom Brady steps out with Bridget Moynahan in N.Y.C.

The Patriots quarterback, fresh off his Super Bowl win, stepped out with Moynahan at the opening of the Ermenegildo Zegna Flagship store in New York City. The couple looked cozy, with Moynahan sporting a white coat with fur trim and Brady in a pin-striped suit. Fellow quarterback Peyton Manning and NFL players Michael Strahan and Jesse Palmer were also at the event.

July 7, 2004: Tom Brady supports Bridget Moynahan at the L.A. premiere of I, Robot

Brady and Moynahan hit the red carpet together at the Los Angeles premiere of her movie, I, Robot. Though the sci-fi thriller (which also starred Will Smith) was packed with tension and crime-committing robots, Brady and Moynahan were all smiles on the red carpet, laughing as they posed together.

July 14, 2004: Bridget Moynahan accompanies Tom Brady to the 2004 ESPYs

It was Moynahan’s turn to support Brady at the 2004 ESPY Awards. Brady was nominated for Best Male Athlete, Best Championship Performance and Best NFL Player. However, he only took home an award with the New England Patriots for Best Game — for their Super Bowl win in February 2004.

June 2005: Tom Brady calls Bridget Moynahan one of his “very best friends” on 60 Minutes

In a rare sit-down interview with 60 Minutes’ Steve Kroft, Brady opened up about his relationship with Moynahan. “She’s helped a lot,” Brady said when Kroft asked if she had helped him settle down.

Brady added: “I can be myself around her, and there’s not many people I can be myself around. It’s fun to be around your best friends who know you well, and she’s someone that I consider one of my very best friends.”

But when asked if marriage was in the couple’s future, Brady deflected. “You can’t ask that,” he responded. “Next question.”

May 1, 2006: Tom Brady and Bridget Moynahan attend the Met Gala together

Brady and Moynahan sported coordinating black ensembles to the 2006 Met Gala, which was themed “AngloMania.” Moynahan kept things simple and chic with a strapless, figure-hugging black dress, while Brady sported a tuxedo with a black velvet jacket.

December 2006: Tom Brady and Bridget Moynahan split up

Moynahan and Brady ended their relationship after three years of dating in December 2006. A rep for Moynahan confirmed the split in a statement to PEOPLE, saying: “(They) amicably ended their three-year relationship several weeks ago. We ask for your respect and consideration of their privacy. No further comments will be made.”

February 18, 2007: Bridget Moynahan is expecting her first child with ex Tom Brady

February 1, 2023: Tom Brady posts a photo with Bridget Moynahan and their son

May 14, 2023: Tom Brady celebrates Bridget Moynahan in an Instagram post

Brady marked Mother’s Day by posting photos of the mothers in his life, including Moynahan, on Instagram. In one picture, Moynahan posed with Brady, their son Jack and Brady’s ex-wife, Bündchen.

“Happy Mothers [sic] Day to all these amazing women who have given our family so much throughout their lives,” the father-of-three wrote in the caption. “Thank you all for your love, compassion and kindness, and for setting such an amazing example for all of our little ones.”